How often does life imitate art in that the first generation goes from rags to riches, second enjoys and adds to the fortune, third dissipates it, and fourth generation is in rags? Or is that just a good novel?

— Posted by Kathy

Not all that often. James Gordon Bennett made a huge fortune in the newspaper business (he more or less invented modern journalism). But after his death in 1872, his son and namesake managed to wreck both the newspaper and the fortune.
But most heirs are less flamboyant than the younger Bennett, and some have been pretty good at money-making themselves. Cornelius Vanderbilt died the richest self-made man in the world in 1877, leaving the bulk of his fortune to his son William Henry Vanderbilt. William doubled the fortune in just eight years.

What does happen is that great fortunes get spread around. We do not have primogeniture in this country, and children tend to be left equal shares. So in a few generations, even the largest fortunes are diminished in this way. The last really rich man named Vanderbilt was Harold Vanderbilt (he invented contract bridge and defended the America’s Cup three times). He was a great-grandson of the Commodore and died in 1970. He had no children and left most of his multimillion-dollar fortune to Vanderbilt University. There is no one named Vanderbilt today who comes anywhere close to being in the Forbes 400, although many of them are still quite comfortable, thank you.

What do you think will happen to “old” money in New York? I have had conversations with private wealth management individuals who indicate that the old money in America tends to invest primarily in domestic concerns, rather than in global opportunities. How does that change when money travels into America from very wealthy families in other parts of the world?

What are some of the peculiar examples of old money wealth in New York’s history that we have forgotten, but that would probably create a valuable lesson for us going forward?

How does one acquire wealth in New York? What is considered the standard for wealth in New York? In other words, what limits does one have to reach in order to be considered wealthy?

— Posted by Pudding

New York, from its very beginnings, has always been a city of the nouveau riche. The so-called Knickerbocker aristocracy that was old money in the first half of the 19th century — with names like Roosevelt, Schuyler, King, Stuyvesant, Lorillard and Schermerhorn — gave way to far larger fortunes of the gilded age, with names like Rockefeller, Astor, Vanderbilt, Gould and Whitney. As Mark Twain put it in 1867, the old Knickerbockers found themselves “supplanted by upstart princes of shoddy, vulgar and with unknown grandfathers. Their incomes which were something for the common herd to gape and gossip about — are merely livelihoods now, would not pay shoddy’s house rent.”

Today, the Astors and Vanderbilt seem like very old money indeed. And, in turn, their fortunes seem small compared with the huge ones created in the last quarter century by people named Gates, Buffett, Dell, Bezos, etc.

Since the 1990s ousted many Harlem and Brooklyn brownstone residents, what’s the current state of black wealth in New York? Is there (still) such a thing? Meaning, does black wealth exist in New York in this day?

— Posted by Cynthia

When I was growing up in Manhattan in the 1950s, the rich lived almost entirely on the East Side, from 59th Street to 96th Street, Fifth Avenue to Third Avenue. There were a few pockets of wealth elsewhere in Manhattan, like Sutton Place, Central Park West. Today, most of Manhattan has been “gentrified,” and that process is spreading to other boroughs. Wealthy black families, because of discrimination, lived mostly in parts of Harlem, like Sugar Hill, and Brooklyn. There is much less discrimination today, so black wealth is less concentrated than it was. But there is much more of it. Until recently, the c.e.o.’s of American Express and Merrill Lynch were both black. I don’t know where they lived, but I doubt it was a third-floor walk-up.

I’d like to know a few things about the future of wealth in New York.

— Posted by Pudding

Well, I’m a historian, not a futurist, but as long as New York remains the extraordinary center of culture and power that it is, the very rich will want to have a presence here.

Manhattan real estate has been one of the greatest investments there has been over the last 50 years, and many rich foreigners, especially those from unstable countries, have invested in it, both to give them a New York residence and a safe haven for part of their money. I would expect that to continue in the future. And as much of the world is getting richer quickly, there will only be more wealthy foreigners looking for high-end New York real estate.

Does the popular TV series “Gossip Girl” accurately portray the wealthy Upper East Side?

— Posted by Jaweed

I’m afraid I don’t know. I’ve never seen it. In fact until I read this question, I’d never heard of it. I’ll check it out.

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